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Five Tools for Happier Growth Conversations

Marcy Swenson
Co-Founder & Executive Coach
Startup Happiness

Marcy is an executive coach, as well as a seasoned technology professional, and a veteran of several successful startups. As a founder at Critical Path, she built the tech team that led to IPO. Forbes named CPTH the fastest growing high tech company in the world in 1999 (3 to 3000 in 4 years). Marcy is a co-founder & executive coach at Startup Happiness, where she helps entrepreneurs with everything from basic leadership skills to deep personal growth.

This was my favorite conference of the year. And by far my favorite conference to speak at today, I want to share with you five tools for happier growth conversations and growth conversations are conversations that all leaders encounter all the time. They're the conversations that happen when someone says.

Hey, what about our promotion? Or when you initiate that conversation and they can be especially tricky for new leaders, right? There really isn't any map. The tools I want to give you today or share with you will be especially helpful for high growth companies. The help you mentor and develop your team.

And what I'm hoping is to avoid the situation where these conversations are done poorly, because that honestly creates a lot of drama and chaos. So these questions are questions that a lot of managers initially dread. They're afraid of maybe doing it wrong. Maybe making promises that they can't keep or even afraid if it's not done well, a person will leave.

But what I've found is that if you can collaborate with someone on their growth and development over the entire time that you're working with them as their manager it can create an incredible. Growth and the people who work for you and a lot of loyalty too. And so all the tools that I'm going to share with you today, you can certainly use when someone approaches you asking for a promotion, but really you should be using them all all the time.

Right. They're all available or all valid to use right now. So first here's a little bit about. I've been an executive coach for the past 13 years, and I mostly work with startup founders. These are logos of some of the companies I've worked with senior execs at, and for the 18 years before that I was a startup founder, myself.

I was in the VP of engineering role. I actually started I was an engineer for my first year. But then we hired three college students and suddenly I became an engineering manager. And that was 30 years ago when there were no blog posts, hardly any books about leadership, especially at small companies.

So I really learned by the seat of my. And so I looked for the tools that I've given to clients that I've worked with and that I've used myself. That'll create the most leverage for you immediately. I want you to have tools that you can go out and use like morning. So here's what we're going to cover.

We're going to cover the ability to listen about too. What people want to grow into with some curiosity. We're going to talk about how the world really works in terms of promotions. I'll share with you a way that I love to use a career ladder. I'll share three of the most commonly coached skills that you'll be likely to coach people on as a new manager.

And then I'll close within individual contributor manager, sorting hat which actually is a kind of nice compare and contrast to the void comp diagram that Nick just shared with you. So let's dive right in. The first skill is listening with curiosity. And when I'm talking with someone about their career, I'm really gonna start by asking very open-ended questions about where they want to.

And what I've found as a coach is that few people are actually listening with true curiosity. Most of us listen, and kind of like wait for the thing that we get to say next. And so if you're able to ask open-ended questions and really listen to what people want and what they're interested in just that is an incredible gift that can build a lot of trust.

And what I find, especially in new leaders is that when they're in these types of growth conversations, they'll either fall into the trap of being too pleased. Right. They'll hear that someone wants a promotion or wants a particular job say, Hey, I'm going to get that for you. We're they'll end up being a little bit to blame.

Right. They'll think like, oh, my job is to keep you from doing that. Or I can't give in too much, you know, I got to make you work for it. And so when you're asking about what someone wants in their career and in their life you can just kind of sit back and listen. So these are the types of questions that I really like to ask people.

You're not really talking about just this promotion, but you're actually talking about like, what do you want in your career? What are you interested in doing? Where do you want to be in five years? 10 years. And as a coach, what I've realized is if I can understand what someone's goals are, I can understand their motivations.

So if I talk to someone in their first year of being an engineer and she says she wants to be a CTO or a CEO someday, that's fantastic because she's going to need to learn a lot of the things in the next few years. Being an engineer that she'll actually be able to use in those other roles. And there might be ways that I can connect her with other resources that will help her learn.

So I really want to know things like that. Now, once I have a better understanding of what this person wants I moved to using this next tool. I want to explain how the world of promotions really works. First I'm going to ask for a show of hands Well, actually one more thing when I'm explaining how the world works in terms of promotions, this isn't really a debate.

It's just an explanation. And a lot of people just kind of don't know this stuff. So first I'm going to ask for a show of hands. How many of you been asked this question? Hey, I've been here for a year now. When do I get a permit? I, I certainly have. What about this question? Like I've been here longer than Steve who just got promoted.

When's it going to be my turn. And how about this one? Sarah has a more senior title, but less experienced than me. What's up. Here's another one that a lot of managers are afraid of. Like, I was just talking with someone earlier this week who said I actually worry the most about people who are thinking, well, why didn't I get another promotion?

I got one last year. Like maybe I shouldn't stay here. Maybe I should just leave, but this person isn't even talking to you. So here's some of the information, that'll start to clear up some of these questions. This image is the top image that comes up when you do a Google search for career ladder.

Like isn't this fascinating. And a lot of people think that this is actually how promotions happen. And what I see when I look at this graphic is that the steps are really small. Super linear. And when I look at this graphic, like if this is all I really had to go on, I would think that promotions happen because time passes, they're going to happen on a really regular cadence and they're going to happen because I have seniority, but really none of those things are true.

Most promotions happen because they're a recognition of someone who's creating more business. That person has built the skills and behaviors. Now they may have been given some opportunities to kind of show off those skills and behaviors, but they have a broader scope of influence. And people are recognizing their ability to create more business value.

And if you can anchor this both in yourself and with the people who work for you it makes these conversations about promotions a lot easier. So let's stick that kind of fake career ladder on a graph. So along the bottom, we have the years of engineering experience and going up, we have business impact and comments, compensation.

A lot of people think this is what a career ladder looks like. This closer to what a career ladder really looks like. And when you look at those little boxes in the lower left, those initial steps are actually really close together and produce. Right. If you get an entry-level job, you probably will get your first promotion in a year, 18 months.

Like it's structured like that. But as you go longer and longer in your career as an engineer, the steps get to have a they get further apart. And the longer distances means that managers actually have to break things into smaller steps to fill the gaps. So another thing you might notice about this career night, your career ladder may have more or less squares and boxes.

But this is kind of a, at least a shape that I'm comfortable showing you. Some of those roles last for the rest of the people's careers, right? Some people start growing and talking. What I want is to help all the people on my team be constantly growing. So if they're capable of doing it, that they can move up the career ladder.

Now there's a second career ladder behind this. It's the one that's in purple and that's actually the manager track and it kind of goes right alongside the IC track. So let's bring that up to the. You can see that first manager role in different companies call it different things. But about your second or third engineering role if you're showing the aptitude for it, you might be offered a team lead or just the beginning manager role.

And notice that's not a promotion, it's a lateral move. And in here, the steps are a lot more even What I will say is when you go from being a manager to actually managing managers, that's actually a big step. And I didn't represent that very accurately on here. Let's see what this also shows is the most, most senior ICS often have higher salaries than the most senior engineering managers, but they're exceptional.

They don't occur in most companies. They're the people who are skilled, like throughout the entire stack or they know a particular architecture just amazingly well and can debunk something on a dime. Anyway, they're exceptionally rare. So here's another point of confusion. It seems like a lot of people seem to volt past each other.

Most often that comes because someone demonstrates the skills and behaviors that are actually needed at the next level. They're actually capable of creating more businesses. But sometimes, especially at startups, they're artifacts of growth. So if someone was hired as an early employee and manager with maybe less experienced than you might've offered them a title that didn't quite make sense, but they used it as a lure to get them in the door.

And those titles will stay around for a long time. They, they came from a time before there was a career ladder at this particular company. But what I'm having those conversations with engineers, I'm less focused on what are the titles other peoples have. I'm more focused on how can I help you create more business value?

So if there's one thing that you take away from this talk it would be the idea that a promotion is a recognition of someone who's able to create more businesses. So just talking about promotions in this way can really be helpful. Now we're going to use a career ladder to actually make this a lot more concrete.

Let's see if a promotion recognizes that you're creating more business value. A career letter is actually a roadmap for how to create that business value. And if your organization, it has a career ladder, that means it's a customized map for how to create more business value. So by all means use it.

And if not, there are several good ones online. The one I'm going to use in this example comes from rent the runway and it's available at this URL. So here's a printout of the very first page of the rent, the runway career ladder. You can see across the top, that's the entry level job there, and that's the first rung of the career ladder.

And then across the middle, that's the second run, the career ladder, and then across the bottom, that's the third. And it's not important to actually read all that. You'll see in a minute what I like to do when I'm talking to someone about like where they are in our organization and what skills they'd like to develop I like to print out their career ladder for, for our particular organization.

And I will give them to, to, to, to, to do these three highlighters. And I'll take the three lessons. And I want them to use green for the skills that they feel like they're super solid on. Like yep, totally got those in spades, yellows like that. I'm learning. I've sorta got that. I need some more practice.

And pink is I'm struggling. I don't understand. I haven't really ever tried this. And I'm gonna fill it out myself, especially if I'm in a new engineering manager, who's actually worked with this person before. Right? A lot of times you were promoted sort of right above your peers. You actually have a good idea of what they know how to do and what they don't.

And other times you might have to ask others, others of their peers to kind of fill in the gaps. So let's say that you give this career ladder to someone who's at that second rung in the ladder who's interested in a promotion or you just want to have a good development conversation with them and you say, okay fill this out, highlight the things that you think you do well, et cetera.

And bring it back to me. Let's say that this is what they bring back. So this could actually be a document created by someone who is super ready for promotion. Right. Absolutely possible. Like here, I'm going to have to use some of my judgment. Another possibility is that it's someone who doesn't have a lot of humility and maybe isn't aware of their blind spots.

Right. That's why I've created kind of my own separate version of it. And so I want to weigh those two things. But here here's kind of the easy example. Let's go to a different one. Let's say again there at the middle rung of the career ladder and they've highlighted these couple of things.

Are they ready for a person emotion? Yeah. Yeah. Honestly, maybe most career ladders have a center of gravity. And the center of gravity is like some really key skill that you've got to master and it's usually creating code of a certain size and a certain complexity, and then collaborating with all the people around you.

So what I want to see us for sure. They've got that. Yeah. Skill. But what's interesting is if they've highlighted in yellow, Some skills in that earlier rung of the career ladder. And we're not at the point in the promotion cycle where I could actually even pitch for them yet. I actually want to help them start developing those skills.

So I was just using this earlier this week with a leader that I coach and we're going through all the people on his team. And so I asked him to fill this out and he had a fairly senior engineer, like in, in this case, he'd be at the maybe fourth or fifth rung of the ladder. And this engineer really had trouble.

Effectively communicating his status to the team, his stand in, stand up and say, well, did this, did this to this, going to do this tomorrow. And it didn't really provide that much business value. And so this leader was able to go back to him and say, Hey, I want to give you feedback on this. You're not able to complete the skill.

And this is actually really early on. We can expect. So it opened up a conversation about what to do the way that I wanted to amend this after listening to Jill's talk was actually recognizing that people in the dominant culture often have let's see. It's often harder for them to see their own flaws.

Right there. They're more used to saying like, yep, I've got it. So if you've got somebody really confident they may give themselves more green. And what I've especially seen with women is that they're more likely to say. Still yellow for me, or, oh, that's really red for me. And so I really want to check, like, is everyone on my team filling this out in the same way?

And I might want to give someone a bump if they're really humble, or if I feel like maybe you're not representing yourselves. Here's a third example. Again, if this was the second level engineer, has this person met the criteria for a promotion? I'm going to say probably not. They've got some key skills that are in red.

My hypothesis might be that this person's new to the team. If this person's been around on the team and these things are actually really important to our organization, this might be a sign that they really need to be on a performance. So I just wanted to give you a sense of how you could use the career ladder, because it can be super confusing as a new manager to give people feedback.

A lot of people come to sync and give me feedback every week. Give me feedback. And instead of giving week by week feedback on things that you may be observed, or maybe you don't have a lot of contact with them, this is a great way to come up with some ideas for development plan and then figure out how you're going to coach them on those things.

And you can pick any one of these things that are in yellow or red, and actually start to dig in and just have a conversation about like, Hey, it looks like you're not able to do this. What's the problem? Where are you getting stuck? How can I help you? And there may be things that we're really good at doing that you can coach them in, or it may be a skill that you don't actually know that well, which case you can hook them up with someone else in their organization who can pair with them or who can teach them the thing they need to know.

Okay. The fourth tool I want to give you is a list of the skills that you're going to coach the most often as a new manager and coaching has become this sort of scary word as if like you need to. A lot of experience to do it. And there are certainly some parts of coaching that are hard and require training and practice.

But what I mean by coaching here is much simpler. These are the things you're going to teach people how to do the first. And I'd love to just be able to like stamp this on everyone's forehead is to have exceptionally clear written and verbal communication. You're going to coach people on this.

The act of figuring out what's in your head that you want to communicate and then figuring out like how, what business value does this have? When should I say it and how should I say it to reach this audience is actually extraordinarily difficult. And so helping people figure this out super important Some of the tools that I really love to do to coach especially verbal communication.

One is actually role-play. So it's saying like, okay, you be, you I'll be the person you are gonna have to talk to try. Tell me what it is you're gonna say. And then to see, like, how does that land in my book? Do I think that actually makes sense and to give them some feedback. And the other thing I'll do, if they're stuck, there is actually model it and say like, okay, let's reverse the roles.

I'll be you, you be the person. And I'll do it a couple of wrong ways and one really kind of gold standard way so that they can kind of got the hang of it.

The second thing you'll have to coach on a lot is intuiting the perspectives and emotions of. This is the ability to see when it's sitting in a meeting room or when I'm sitting across from one person what's in their head what are the emotions that are showing up in them and what is the impact I'm having on them or what is the impact that other people are having on them?

And what I find really interesting about this, and I just learned it in a neuroscience class earlier this year is this can be particularly difficult or. Been particularly difficult for some white men to learn because it's a skill that most people learn when they need to. And most people who don't have an inherent sense of safety and that includes, you know, women, people of color, like other marginalized groups learn this early on in their lives for their own stuff.

People can also learn this in really difficult family situations. But there are men that I've worked with who literally just don't have a really good understanding of what the perspectives of the people across from them are. And it actually shows up as a almost a form of a hand. And so the ability to teach someone to learn that or teach someone to be able to do that can be incredibly helpful as manager.

And the way that I like to do that is actually by asking. So what do you think so-and-so was thinking in that meeting? Why do you think they said the thing that they did and ask the person to make educated guesses and then I'll start to sort of train their guesses and say, Hmm. Here's where I thought that they were.

They were thinking or here's why I thought they said that. And what I want them to be able to do over time is to both pay attention to it, to be able to read body language and cues. But also to just be thinking about it regularly, and most people will get better at it. My experience has been, it's actually within like three to six months, if they're really picking it.

The third thing is prioritization and time management. And so this is something that especially early on in people's careers they'll get modeled on and prioritization. I like to think of as organizing the things on your to-do list in order of what will create the most business. And so part of this is knowing like what's valuable to the business, but the other part is like putting things in order and being willing to say no to the things that are at the bottom of the list.

And my favorite tool for doing both of these as a coach is actually to have someone take out a pen pen and write down what are all the things you think are on your to-do list. And now let's look at all these things. And see, is this actually practical? Like could any human do all these things? And if it's a no.

Okay. Where do we need to draw the dividing line so that you can actually like, say for real, as you can get this done, and then what are we going to do about all the things that are below the line? And you can do this with meetings on people's calendars. Right. You can say like, all right, let's write down every meeting on your calendar for a week that recurs which provide the most business value, right.

Top to bottom. As we write them all down, how many hours of meetings can you actually not just tolerate, but makes sense to you. And let's draw a line under those and kind of leave out the rest of them.

My final one. Final tool is the IC manager, sorting hat. And this is a way that I have found really works in helping soar individual contributors for managers. And this can help you resolve the question of someone coming in your office saying like, Hey, I think I might want to be a manager, or you being able to tap someone on the shoulder and say, Hey, I think he would make a really good manager.

So here's the first piece of the tool. I want to know, does this person see the world more through the lens of. Bits and procedures and code, or did they see people see the world war through the lens of people? This is going to be a big switch for them. And for most individual contributors, the procedures and code is way in the forefront, the people's way in the background.

And then as they get further in their career, the people tends to. Because they do things in bigger groups. And so they actually have to build a lot better people skills. For managers within the first year of being a manager, the people skills has to move to the forefront because they're really mostly responsible for, for people and relationships and building a team.

And so usually the code really drops into the background and the people move much into the fourth. The second part of the test is to ask them what books they like to read. If they really love reading books about code. That's useful information. If they like reading any of these excellent books about management that's also useful information and if they've never read one of the books about management I'm happy to buy them one and hand it to them and say, go read this over the weekend and come back and discuss it with me.

And I want to see the level of richness of the discussion and whether they're really grooving on it, or whether it felt like kind of a mean assignment. And. And just for fun, there's two fake books on this slide.

The other test I'll use is do they themselves have the top three skills that I think they're going to end up coaching as managers, right? Did they have clear written and verbal communication? Are they good at intuiting, the perspectives and emotions of others. And are they decently good at their own time management and prioritization?

They're going to coach these all the time and they're going to need to model them. So I want to know that they're going to do them well. Here's another test. I asked them to describe their college. And I don't give them any direction. Other than that, just like, describe your colleagues to me. What I want to hear is are you describing them as being particularly good at languages or tasks, or are you describing anything about their in their inner world?

Are you actually talking about what this person believes, loves yearns for? Doesn't like to do what upsets them. Like they need to have some sort of picture of the people around them and what's going on inside of them. And if they don't, but they're still saying like, oh, I really want to be a manager.

And it's like, great. Go out for a week. Start to pay attention to people's inner world. Come back with more information. Like, let's talk about that. Let's see if I can teach you how to do that. The final test is I'll ask them about a meeting relatively recent. That was kind of difficult. And I'll ask them what was happening in there.

Like what would you have done differently? How would you have improved this? Because I know they're going to end up in meetings without me, where they're actually going to have to solve problems in real time between other humans. So I want to see that they can understand what's happening and that they have ideas for how they would make them better.

So here's what we've run through today. We've talked about like live listening to the stance of curiosity and really coming to know what someone wants to do explaining to them how the world of promotions works which is incredibly nuanced. So I just gave you this, like very almost a surface level understanding.

We talked about using a career ladder. And coloring them all in how to coach some top skills and the manager icy, sorting hat. But if there's one thing I would leave you with too. I hope it's this that the thing that you want to emphasize with the people who work for you is their career success is going to depend on their ability to create more business value.

Like not just in this role today and in this company, but like over the entire span of their career. So I hope that you'll be able to use these tools to help those growth conversations go better to have good conversations. And that far from being scary, they actually did. Really good learning and growth.

You can see all my slides and download this presentation at my website, startup happiness. And by the way, all the tools that I talked to you about today for using with your direct reports are all tools that you can use with yourself. So looking at your company's manager career ladder and figuring out like, okay, what are the different things I can highlight so that I can advance myself totally worth it.

Thanks so much. Totally a pleasure to talk to you. .

About Calibrate—

Founded in 2015, Calibrate is a yearly conference for new engineering managers hosted by seasoned engineering managers. The experience level of the speakers ranges from newcomers all the way through senior engineering leaders with over twenty years of experience in the field. Each speaker is greatly concerned about the craft of engineering management. Organized and hosted by Sharethrough, it was conducted yearly in September, from 2015-2019 in San Francisco, California.